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Synthesis method of octahydro-4a,8-epoxypyrido[4,3-c]azepine-6(5h)-tert-butyl carboxylate

A technology of tert-butyl formate and epoxy pyridine is applied in the field of chemical synthesis to achieve the effects of saving raw material cost, shortening synthesis route and ingenious reaction design

Active Publication Date: 2022-04-12
WUXI APPTEC +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the synthesis method of octahydro-4A,8-epoxypyrido[4,3-C]azepine-6(5H)-tert-butyl carboxylate is rarely reported in the literature

Method used

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  • Synthesis method of octahydro-4a,8-epoxypyrido[4,3-c]azepine-6(5h)-tert-butyl carboxylate
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  • Synthesis method of octahydro-4a,8-epoxypyrido[4,3-c]azepine-6(5h)-tert-butyl carboxylate

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Embodiment 1

[0066]

[0067] Step 1: A catalytic amount of osmium tetroxide was added to a solution of compound 1 (24.6 g, 86 mmol) and NMO (15 g, 129 mmol) in acetone (500 mL) at room temperature, and stirred at room temperature for 4 hrs. TLC (ethyl acetate) monitoring showed that the reaction was complete, water (500 mL) was added to the reaction system, extracted with ethyl acetate (500 mL x 3), the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain compound 2 (27 g, 84.6 mmol) of the crude product was used directly in the next step.

[0068] Step 2: Dissolve compound 2 (27g, 84.6mmol) in a mixed solvent of methanol (450mL) and water (50mL) at room temperature, add sodium periodate (27g, 127mmol), and stir at room temperature for 4hrs. TLC (ethyl acetate) monitoring showed the reaction was complete. Add water (500mL), extract with dichloromethane (500mL x 3), combine the organic phases, dry with anhydrous sodium ...

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Abstract

The invention discloses a synthesis method of octahydro-4A,8-epoxypyrido[4,3-C]azepine-6(5H)-tert-butyl formate, comprising the following steps: the first step, compound 1 React with a catalytic amount of osmium tetroxide and the first oxidant to obtain compound 2; in the second step, compound 2 oxidizes the alcoholic hydroxyl group to an aldehyde group under the action of the second oxidant to obtain compound 3; in the third step, compound 3 and benzylamine are Reductive amination under inert atmosphere and first reducing agent effect, obtains compound 4; In the fourth step, compound 4 is in Boc 2 Catalytic hydrogenation with palladium catalyst in the presence of O to obtain compound 5; in the fifth step, compound 5 was reduced with a second reducing agent to obtain compound 6; in the sixth step, compound 6 was catalytically hydrogenated under the action of a palladium catalyst to obtain compound 7. The method of the invention has the advantages of easy to obtain raw materials, convenient operation, safe reaction, suitable for scale-up, short route, high overall yield, suitable for industrial production and the like.

Description

technical field [0001] The invention relates to the field of chemical synthesis methods, in particular to a method for synthesizing octahydro-4A, 8-epoxypyrido[4,3-C]azepine-6(5H)-tert-butyl carboxylate. Background technique [0002] The compound octahydro-4A,8-epoxypyrido[4,3-C]azepine-6(5H)-tert-butyl carboxylate (CAS: 1251010-89-5) and related derivatives in Medicinal Chemistry It has wide applications in organic synthesis. Currently, there are few reports on the synthesis of octahydro-4A,8-epoxypyrido[4,3-C]azepine-6(5H)-tert-butyl carboxylate. [0003] Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0004] The technical problem to be solved by the present invention is to provide a method for synthesizing octahydro-4A, 8-epoxypyrido[4,3-C]azepine-6(5H)-carboxylic acid tert-butyl e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/18
CPCC07D498/18
Inventor 周强张大为孙春于凌波徐学芹毛延军董径超马汝建徐艳白有银兰倩倩高明飞姚宝元赵廷巴苏伟刘双燕
Owner WUXI APPTEC